Esterification of 2-(4-(4-Hydroxy-3, 5-Iiodophenoxy)-3, 5-Diiodophenyl) Acetic Acid (Tetrac)

Abstract

Tetrac, a deaminated derivative of the thyroid hormome, has received some broad interest for its ability to inhibit the spread of new blood vessels, i.e., angiogenesis. For an optimum activity, the action of the dug shall be limited at the cell surface for interaction with the integrin alpha v beta 3. This was shown to be achieved via a nanoparticle formulation that would be grafted to Tetrac phenol’s OH. While the principle of this study has been disclosed elsewhere, the broad results have never been disclosed entirely. Here all outcomes of the synthesis strategy, e.g., protection and activation steps, confirmed Triisopropylsillyl as a protective group of choice to access the nanoparticle. Catalyst assisted esterification has been probed and discussed. Then the HPLC-MS study allowed to clarify reaction conditions that could subsequently yield to the desired activated Tetrac moiety. The reaction products were all characterized by 1H and 13C-NMR.